3'-Deoxy-3'-hydroxymethyl-aldopentopyranosyl nucleoside synthesis. Part I

Article abstract of DOI:10.1016/0040-4020(95)00211-P

A straightforward synthesis of 3'-deoxy-3'-hydroxymethyl-aldopentopyranosyl nucleosides is described starting from β-D-xylopyranosyl nucleosides. β-D-xylopyranosyl thymine 17a,b,c, and uracil 17d are converted into the 4'-benzoylated derivatives 18a,b and further into the 2',3'-enepyranosyl compounds 19b,c. A 3'-hydroxymethyl appendix has been introduced using a free-radical methodology to furnish 20a,b. Inversion of configuration of the 4'-position yielded the target nucleosides 22a,b. X-ray and ¹H NMR conformation analysis prove the equatorial orientation of the base moiety in the target compounds.